(3R,5R)-9-(benzyloxy)-3-methylnon-1-en-7-yn-5-yl N-[(tert-butoxy)carbonyl]-N-methyl-D-phenylalaninate

Base Information

• Chemical Name: (3R,5R)-9-(benzyloxy)-3-methylnon-1-en-7-yn-5-yl N-[(tert-butoxy)carbonyl]-N-methyl-D-phenylalaninate
• CAS No.: 1472660-27-7
• Molecular Formula: C₃₂H₄₁NO₅
• Molecular Weight: 519.681
• Mol file: 1472660-27-7.mol

Synonyms:(3R,5R)-9-(benzyloxy)-3-methylnon-1-en-7-yn-5-yl N-[(tert-butoxy)carbonyl]-N-methyl-D-phenylalaninate

Chemical Property of (3R,5R)-9-(benzyloxy)-3-methylnon-1-en-7-yn-5-yl N-[(tert-butoxy)carbonyl]-N-methyl-D-phenylalaninate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,5R)-9-(benzyloxy)-3-methylnon-1-en-7-yn-5-yl N-[(tert-butoxy)carbonyl]-N-methyl-D-phenylalaninate

There total 18 articles about (3R,5R)-9-(benzyloxy)-3-methylnon-1-en-7-yn-5-yl N-[(tert-butoxy)carbonyl]-N-methyl-D-phenylalaninate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 65.0%

(3R,5S)-9-(benzyloxy)-3-methylnon-1-en-7-yn-5-ol (1472659-99-6) + N-tert-butoxycarbonyl-N-methyl-D-phenylalanine (37553-65-4,64263-83-8,85466-66-6) → (3R,5R)-9-(benzyloxy)-3-methylnon-1-en-7-yn-5-yl N-[(tert-butoxy)carbonyl]-N-methyl-D-phenylalaninate (1472660-27-7)

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 - 20 ℃; for 10h; Inert atmosphere;

DOI:10.1002/hlca.201200519

Reference yield:

(2R,4S)-8-(benzyloxy)-2-methyloct-6-yne-1,4-diol (1472660-18-6) → (3R,5R)-9-(benzyloxy)-3-methylnon-1-en-7-yn-5-yl N-[(tert-butoxy)carbonyl]-N-methyl-D-phenylalaninate (1472660-27-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane; water / 3 h / 20 °C

2.1: diisobutylaluminium hydride / dichloromethane / 0.5 h / -78 °C / Inert atmosphere

3.1: sodium hexamethyldisilazane / tetrahydrofuran; toluene / 0.5 h / -78 °C / Inert atmosphere

3.2: 5 h / -78 - 0 °C / Inert atmosphere

4.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 10 h / 0 - 20 °C / Inert atmosphere

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; di-isopropyl azodicarboxylate; sodium hexamethyldisilazane; diisobutylaluminium hydride; triphenylphosphine; In tetrahydrofuran; dichloromethane; water; toluene; 3.1: |Wittig Olefination / 3.2: |Wittig Olefination;

DOI:10.1002/hlca.201200519

Reference yield:

(3R,5S)-5-[4-(benzyloxy)but-2-yn-1-yl]-3-methyldihydrofuran-2(3H)-one (1472660-20-0) → (3R,5R)-9-(benzyloxy)-3-methylnon-1-en-7-yn-5-yl N-[(tert-butoxy)carbonyl]-N-methyl-D-phenylalaninate (1472660-27-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: diisobutylaluminium hydride / dichloromethane / 0.5 h / -78 °C / Inert atmosphere

2.1: sodium hexamethyldisilazane / tetrahydrofuran; toluene / 0.5 h / -78 °C / Inert atmosphere

2.2: 5 h / -78 - 0 °C / Inert atmosphere

3.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 10 h / 0 - 20 °C / Inert atmosphere

With di-isopropyl azodicarboxylate; sodium hexamethyldisilazane; diisobutylaluminium hydride; triphenylphosphine; In tetrahydrofuran; dichloromethane; toluene; 2.1: |Wittig Olefination / 2.2: |Wittig Olefination;

DOI:10.1002/hlca.201200519

upstream raw materials:

(2R,4S)-8-(benzyloxy)-2-methyloct-6-yne-1,4-diol

(3R,5S)-5-[4-(benzyloxy)but-2-yn-1-yl]-3-methyldihydrofuran-2(3H)-one

(3R,5S)-9-(benzyloxy)-3-methylnon-1-en-7-yn-5-ol

N-tert-butoxycarbonyl-N-methyl-D-phenylalanine

Downstream raw materials:

(3R,5R)-9-(benzyloxy)-3-methylnon-1-en-7-yn-5-yl N-methyl-D-phenylalaninate

(3R,5R)-9-(benzyloxy)-3-methylnon-1-en-7-yn-5-yl N-[(2S,4R)-2,4-dimethylhex-5-enoyl]-N-methyl-D-phenylalaninate

(3R,6S,8R,11R,13R)-3-benzyl-13-[4-(benzyloxy)but-2-yn-1-yl]-4,6,8,11-tetramethyl-1-oxa-4-azacyclotridec-9-ene-2,5-dione